Issue 5, 2022

The syntheses, structures and spectroelectrochemical properties of 6-oxo-verdazyl derivatives bearing surface anchoring groups

Abstract

A series of 6-oxo-verdazyl radicals functionalised at the 1- and 5-positions by tolyl, thioanisole and iodophenyl groups were synthesised using conventional strategies. Facile Sonogashira cross-coupling reactions of terminal alkynes with the diiodo derivative were used for synthetic elaboration of the verdazyl core structure with π-conjugated ethynyl groups. The radicals were characterised by EPR spectroscopy, single-crystal X-ray diffraction, cyclic voltammetry and optical spectroscopy. The chemically and electrochemically reversible oxidation and reduction of these radicals within a convenient redox window permitted further studies on the closed-shell cationic and anionic forms using spectroelectrochemical methods, supported by (TD-)DFT calculations.

Graphical abstract: The syntheses, structures and spectroelectrochemical properties of 6-oxo-verdazyl derivatives bearing surface anchoring groups

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2021
Accepted
15 Dec 2021
First published
21 Dec 2021

J. Mater. Chem. C, 2022,10, 1896-1915

The syntheses, structures and spectroelectrochemical properties of 6-oxo-verdazyl derivatives bearing surface anchoring groups

V. J. Kumar, J. Wu, M. Judd, E. Rousset, M. Korb, S. A. Moggach, N. Cox and P. J. Low, J. Mater. Chem. C, 2022, 10, 1896 DOI: 10.1039/D1TC05495C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements